The Oversized Clothes Trend Is A Genius Winter Styling Hack

If the last few months haven't convinced you that oversized clothes are back in style, then we bet that Rihanna's Halftime Show at the Super Bowl LVII on February 12 definitely did. The singer and entrepreneur looked amazing in a red ensemble that featured an Alaïa puffer coat with Loewe jumpsuit and bustier (an outfit that paid tribute to the late Vogue creative director and editor-at-large André Leon Talley). Not to mention the fact that her backup dancers were in oversized sweatsuits and puffer jackets.

We all know that layers keep us warm, but it's hard to have as much confidence as Rihanna when we feel like the "Could I be wearing anymore clothes?!" scene fromFriends. How are we supposed to show off our personal style when we can barely see our faces under all the coats, scarves, and hats?

We turned to former fashion editor turned entrepreneur Alyssa Coscarelli, who dreams up limited edition collabs with emerging makers, andKate Bauer, who expertly turns thrifted pieces into colorful, one-of-a-kind outfits, for answers.

They're here to breakdown your misconceptions about oversized clothes, and how you can style them to reflect your personal style. The first item on their agenda? Throw out the idea that someone can't wear the trend because they think it doesn't flatter their body type.

"I’m less concerned with labeling 'body types' these days because I think a lot of fashion rules are out the window (in a good way), plus even within typical 'body types' there is so much variation individual to individual," says Coscarelli.

"I have been working on releasing myself from the myth that outfits have to be 'flattering' to make me feel good and stylish," says Bauer. "Before, I used to make sure I balanced an oversized top or bottom with a fitted element in order to accentuate a waistline. But the right boxier pieces can work together!"

"My favorite thing about the oversized trend is not having to get things tailored," Coscarelli adds. "As a petite consumer myself, I make frequent trips to the tailor to get things taken in and up. But with the oversized trend, I can style larger pieces in a way that makes them feel intentional rather than ill-fitting. I try to channel my Mary-Kate and Ashley Olsen and just roll with the oversized vibe."

We're down to try anything that lets us channel the Olsen twins. Keep reading for the best tips on styling layers that keep you warm without veering off into Michelin Man territory.

How To Know Proportions For Your Body

Rather than dressing for a generalized body type (like petite, tall, or plus), it's important to remember that everyone's body is different. That means you should be dressing for your body and what fits you best.

Coscarelli says experimentation is key. "Just have fun with experimenting with your inseams, rises, and overall silhouettes and you will slowly gain an understanding of what makes you look the way you want to look — even if it’s not what’s traditionally 'flattering,' because I think that term can often just enforce outdated ways of thought when it comes to our bodies and how they’re shaped."

What's The Difference Between Baggy And Oversized Clothes?

Wearing an oversized piece of clothing doesn't mean that it's too big for you. When shopping for pieces that are designed to look large, it's important to keep an eye on whether the proportions still fit.

"When wearing baggy/boxy styles, other elements of fit beyond body shape become more important: how do the shoulder seams fit me? Where do the pants or skirt hit at my ankles?" Bauer says. "The key is making sure the pieces look intentionally oversized, not like they're the wrong size."

For oversized pieces, you'll still order your regular size to keep those proportions equal. If you want a baggy look, order a regular item that's one or two sizes larger than your normal size.

"An oversized blouse where the shoulder seams match your shoulders (and aren't dropped halfway down your biceps) add intentionality," Bauer adds. "A boxy pant that leaves space at the bottom for a cute shoe or loafer immediately make a baggy-on-baggy look feel elevated."

How Do You Pick What Clothes To Wear?

A few years ago, we would have recommended only picking one oversized item at a time, but these days, it's normal to go wild with as much volume as you want! Whether you're wearing a prairie dress with a big coat or an oversized sweatshirt and loose-fitting jeans, you can mix and match pieces and styles to create something totally your own.

"I think we are living in a paradigm shift in terms of what people, especially women, are hoping to feel when we get dressed. There's a lot of talk on social media about whose 'gaze' dictates fashion choices [and] the 'female gaze' tends to refer to dressing for joy, comfort, self-expression (ie. outside of what is conventionally considered 'attractive')," Bauer says. "Now this obviously is an oversimplification of the very complex act of getting dressed, and I don't want to reduce everybody's outfit choices to this binary. But oversized clothes [make me] feel empowered, interesting, and they feel fashionable without needing to highlight the shape of my body. Plus — COMFORT!"

What Oversized Pieces Look The Best?

If you're new to the oversized clothing trend, opt for pieces that always look good oversized to start. Pullovers, blazers, tees, and coats are all having their own oversized moment and you can't go wrong with any (or all) of them.

What Colors Should I Be Looking For?

"I’m typically all about color, but when it comes to shopping oversized I tend to gravitate to neutrals like grey, black, and tan, because I think it can be nice to offset a more oversized silhouette with a more muted, minimal tone (which I can’t believe I’m saying, because I love color! — but this does stand true)," Coscarelli says.

If you want to experiment with sizes more than colors, stick to neutrals or find one piece that you want to accentuate, like a multicolored pullover with a neutral dress. Want to really make a statement? Make sure every piece of your outfit is a different color.

"I shop with my gut, and I know which colors fit my wardrobe! I don't think there are rules per se — if you're new to wearing oversized silhouettes, go for colors and patterns that already feel like 'YOU'!" Bauer says. "If you wear a lot of neutrals, a mid wash baggy denim or a long and boxy white blouse are great places to start."

How Do I Wear Oversized Clothes With My Winter Gear?

Belts and scarves can help visually break up an outfit, but adding structure with different silhouettes and lengths — like a straight coat with defined shoulders on top of a loose sweater instead of a short, round teddy coat on top of a short sweater — will offer some variety.

"I try not to put anything oversized over anything super bulky, which may sound counterintuitive (because with an oversized coat you might feel like you have room to layer up!) — but I think oversized shapes sit well on tighter layers, and sometimes I like to let a little leg or shape peek out from underneath oversized outerwear," Coscarelli says.

She also recommends getting some good heat tech: "You can’t go wrong with tight-fitting turtlenecks or layers underneath more oversized clothing for added dimension and warmth without the bulk."

"In the winter, anything goes," Bauer says. "It's nice to see warmth is trending these days — cozy sweaters, big coats, etc. Accessorizing intentionally is a great way to make sure you don't get swallowed in a lot of winter clothes — fun sunglasses or a bright bag are what I always reach for when I'm feeling like my layers are taking over."